30 most shocking moments in late night history
By Jeremy Dick
20. Sarah Silverman “confesses” to cheating on Jimmy Kimmel
In 2008, actor Matt Damon was the butt of a long-running joke on Jimmy Kimmel Live! with the idea that Kimmel would always “run out of time” before getting to his interview with Damon. Usually, Damon would retort that he would get his revenge for constantly being direspected by Kimmel, and with the help of Sarah Silverman— Kimmel’s girlfriend at the time— he finally managed to do just that.
How can you make the sting of being cheated on hurt that much worse? Why, you have the cheater do a song on national television about it, of course! As you can guess, that’s precisely what happened. Silverman appeared with Damon on an episode of Jimmy Kimmel Live! to confess that she has been “cheating” on Kimmel with his arch-nemesis Matt Damon, and that she wrote a song about the whole thing.
It was all unexpected, especially for Kimmel himself, who appeared to be seething inside despite his forced smiles. Some fans in the audience probably wondered if the two were crossing a line with the joke. But seeing Damon dancing to the tune of Kimmel’s girlfriend talking about hooking up with him made for one of the most entertaining moments in the show’s history.
Next: 19. How to become a U.S. citizen